Piperidine → N-(2,4-Dimethoxybenzyl)pyrimidin-4-amine

HRID 337728

Reaktionsgleichung

Reaktionsgleichung von HRID 337728
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][N:3]=1.[CH3:8][O:9][C:10]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:11]=1[CH:12]=O.N1CCCCC1.[BH4-].[Na+]>C1(C)C=CC=CC=1.O>[CH3:8][O:9][C:10]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:11]=1[CH2:12][NH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][N:3]=1

Komponenten

7

Edukt 4

HCID 8082PiperidineHCID 689584-AminopyrimidineHCID 691752,4-DimethoxybenzaldehydeHCID 4311764Sodium borohydride

Produkt 1

HCID 63362995N-(2,4-Dimethoxybenzyl)pyrimidin-4-amineAusbeute 52,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 4-aminopyrimidine (20.0 g, 210 mmol), 2,4-dimethoxybenzaldehyde (69.9 g, 421 mmol) and piperidine (2.08 mL, 21.0 mmol) in toluene (1 L) was stirred for 7 hours under reflux, and the solvent was subjected to azeotropic distillation with water. After allowing to cool, the reaction solution was diluted with ethanol (500 mL). Sodium borohydride (7.96 g, 210 mmol) was added thereto with cooling on ice, and the mixture was stirred at room temperature for 16 hours. To the reaction solution, water (500 mL) was added, and an organic layer was extracted. The thus obtained organic layer was dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography (ethyl acetate/methanol=95:5) to yield the title compound (27.0 g, 52%) as a colorless solid.

Aufarbeitung

  1. temperatureunder reflux
  2. distillationthe solvent was subjected to azeotropic distillation with water
  3. temperatureto cool
  4. additionthe reaction solution was diluted with ethanol (500 mL)
  5. temperaturewith cooling on ice
  6. extractionan organic layer was extracted
  7. dry with materialThe thus obtained organic layer was dried over anhydrous sodium sulfate
  8. concentrationAfter vacuum concentration
  9. customthe residue was purified with silica gel chromatography (ethyl acetate/methanol=95:5)

Quellen und Nachweise

ORD-Eintrag
ord-9da8027bd5b44ede81a610d6f916a157
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889741B2

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